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New two-step sequence involving a hetero-Diels–Alder and a nonphenolic oxidative coupling reaction: a convergent access to analogs of steganacin

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Title: New two-step sequence involving a hetero-Diels–Alder and a nonphenolic oxidative coupling reaction: a convergent access to analogs of steganacin
Authors: Laurent, Mathieu Y. mathieu.laurent@univ-lemans.fr, Stocker, Vivien1, Temgoua, Valéry Momo1, Dujardin, Gilles1, Dhal, Robert1
Source: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Apr2011, Vol. 52 Issue 14, p1608-1611. 4p.
Subjects: Diels-Alder reaction, Phenols, Oxidation-reduction reaction, Furans, Antimitotic agents, Stereochemistry, Lignans
Abstract: Abstract: A new family of analogs of steganacin, an important antimitotic compound, was accessed. It takes advantage of a completely stereoselective sequence of two key steps. The central dihydropyrane core is built by a highly diastereoselective and facially controlled hetero-Diels–Alder reaction. It is followed by a nonphenolic biaryl oxidative coupling with a complete atropo-stereoselectivity. It leads to a quick way to form cyclic biaryl lignans. [Copyright &y& Elsevier]
Copyright of Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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DbLabel: Engineering Source
An: 59170047
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PubType: Academic Journal
PubTypeId: academicJournal
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  Data: New two-step sequence involving a hetero-Diels–Alder and a nonphenolic oxidative coupling reaction: a convergent access to analogs of steganacin
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  Data: <searchLink fieldCode="JN" term="%22Tetrahedron+Letters%3A+International+Organ+for+the+Rapid+Publication+of+Preliminary+Communications+in+Organic+Chemistry%22">Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry</searchLink>. Apr2011, Vol. 52 Issue 14, p1608-1611. 4p.
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  Data: <searchLink fieldCode="DE" term="%22Diels-Alder+reaction%22">Diels-Alder reaction</searchLink><br /><searchLink fieldCode="DE" term="%22Phenols%22">Phenols</searchLink><br /><searchLink fieldCode="DE" term="%22Oxidation-reduction+reaction%22">Oxidation-reduction reaction</searchLink><br /><searchLink fieldCode="DE" term="%22Furans%22">Furans</searchLink><br /><searchLink fieldCode="DE" term="%22Antimitotic+agents%22">Antimitotic agents</searchLink><br /><searchLink fieldCode="DE" term="%22Stereochemistry%22">Stereochemistry</searchLink><br /><searchLink fieldCode="DE" term="%22Lignans%22">Lignans</searchLink>
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  Data: Abstract: A new family of analogs of steganacin, an important antimitotic compound, was accessed. It takes advantage of a completely stereoselective sequence of two key steps. The central dihydropyrane core is built by a highly diastereoselective and facially controlled hetero-Diels–Alder reaction. It is followed by a nonphenolic biaryl oxidative coupling with a complete atropo-stereoselectivity. It leads to a quick way to form cyclic biaryl lignans. [Copyright &y& Elsevier]
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  Data: <i>Copyright of Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1016/j.tetlet.2011.01.097
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        Text: English
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      – SubjectFull: Phenols
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      – SubjectFull: Lignans
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              Text: Apr2011
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